With the rise of hedge funds and other sophisticated investment strategies, the financial industry now seeks to perform analysis across a wider variety of asset classes, hedges relevant to particular assets, positions, sectors and markets, and on lesser-known relationships between or among these categories. Positions now include complex and sometimes multiple derivative hedges to mitigate risk. Derivative values decay over time and have various triggers and maturities. Thus, while the instruments and hedging techniques have become markedly more complex, existing portfolio and risk management tools lack the capability to properly assess the diversification of these complex positions, as well as the changing impact of external factors, and lack the ability to provide accurate high level views of performance and risk. In addition, due to the complexities of monitoring and managing these investments, it is challenging to identify new investments that will provide diversification benefits to the portfolio. Conventional risk assessment tools typically perform analysis on the current portfolio based on historical asset or securities relationships. These tools often rely on unstable factors that incorrectly assume that the future will look nearly identical to the past, giving a false sense of confidence in the riskiness and diversification of a dynamic portfolio that incorporates derivative instruments.